WO2011055732A1 - Method for reducing chloropropanols and chloropropanol-forming substances in glyceride oil or fat - Google Patents

Method for reducing chloropropanols and chloropropanol-forming substances in glyceride oil or fat Download PDF

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WO2011055732A1
WO2011055732A1 PCT/JP2010/069548 JP2010069548W WO2011055732A1 WO 2011055732 A1 WO2011055732 A1 WO 2011055732A1 JP 2010069548 W JP2010069548 W JP 2010069548W WO 2011055732 A1 WO2011055732 A1 WO 2011055732A1
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fat
glyceride
oil
sfc
chloropropanols
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PCT/JP2010/069548
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French (fr)
Japanese (ja)
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雅充 栗山
陽子 黒澤
仁美 尾森
暁 森田
朋美 井上
太 横溝
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不二製油株式会社
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Priority to JP2011539373A priority Critical patent/JPWO2011055732A1/en
Publication of WO2011055732A1 publication Critical patent/WO2011055732A1/en

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases

Definitions

  • the present invention relates to a method for reducing chloropropanols and substances forming the same in glyceride oils and fats.
  • Chloropropanol is a general term for substances in which chlorine is bonded to propanol, but 3-chloropropanediol, which is one of these substances, has conventionally been produced in small quantities as a by-product when mainly producing amino acid solutions such as soy sauce. In addition, it is said that it is formed by the presence of lipids and salt in the process of cooking food.
  • Non-Patent Document 1 Korean Patent Document 1
  • Non-Patent Document 2 glycidol fatty acid esters are present as forming substances in the process of producing chloropropanols in glyceride oils.
  • An object of the present invention is to provide a method for reducing chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester and glycidol fatty acid ester which is a forming substance thereof.
  • the present inventors can reduce chloropropanols and their forming substances in glyceride oils and fats by purifying glyceride oils and fats that have undergone decolorization and deodorization processes after contacting with an alkaline aqueous solution. As a result, the present invention has been completed.
  • the present inventors contacted a glyceride oil / fat that has undergone decoloring and deodorizing processes with a solid alkaline substance having a weight ratio of 150 to 750 ppm, and SFC (20 ° C. and / or 35 ° C.) of the obtained oil / fat.
  • SFC 20 ° C. and / or 35 ° C.
  • the first of the present invention is a method for reducing chloropropanols and their forming substances in glyceride fats and oils, wherein the glyceride fats and oils that have undergone decoloring and deodorizing steps are purified after contacting with an alkaline aqueous solution.
  • the second is the method described in the first, wherein the glyceride oil is purified at 230 ° C. or lower after contact with the alkaline aqueous solution.
  • the third method is either the first method or the second method in which the glyceride fat is washed with water after the contact with the alkaline aqueous solution and before purification.
  • a solid alkaline substance with a weight ratio of 150 to 750 ppm is brought into contact with the glyceride fats and oils that have undergone the decoloring and deodorizing steps, and the SFC (20 ° C and / or 35 ° C) of the resulting fats and oils is brought into contact with the solid alkaline substances
  • SFC Solid Fat Content / solid fat index
  • the fifth is the method according to the fourth, wherein the solid alkaline substance is in the form of a powder containing 60% by weight or more of particles having a particle diameter of 1.2 mm or less.
  • 3-chloropropanediol and 3-chloropropanediol fatty acid ester which are chloropropanols in glyceride fats and oils, and glycidol fatty acid ester which is a forming substance thereof can be reduced.
  • oils and fats used in the present invention include soybean oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, rice bran oil, safflower oil, safflower oil, olive oil, sesame oil, palm oil, palm oil, palm kernel oil and other plants.
  • Oils and fats such as beef tallow and pork tallow, and processed oils and fats that have been subjected to separation, hydrogenation, transesterification, etc., or a combination of these. Among them, among these, it can be preferably applied to palm oils.
  • alkali metal or alkaline earth metal hydroxides and carbonates can be used, and specifically, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate. Sodium hydrogen carbonate or the like can be used.
  • alkaline agents may be those generally used for foods and pharmaceuticals, and may be used alone or in combination of two or more. Among these, sodium hydroxide is preferably used.
  • a glyceride fat is purified after contacting with a sodium hydroxide aqueous solution
  • a prescribed amount of the sodium hydroxide aqueous solution is added to the glyceride fat heated to 70 ° C., and the oil layer is dehydrated after stirring and centrifuging.
  • chloropropanols and their forming substances in glyceride fats and oils can be reduced.
  • the method of the present invention preferably further performs decolorization and deodorization purification after contact with the aqueous alkali solution.
  • the purification step at this time is carried out at 230 ° C. or lower, the chloropropanols in the glyceride oil and fat and its The effect of reducing the forming substance is obtained, which is preferable.
  • the method of the present invention can further reduce chloropropanols and substances forming the same in glyceride fats and oils by washing with an aqueous alkali solution and before purification.
  • alkoxide compounds alkali metal or alkaline earth metal hydroxides, and carbonates
  • sodium methoxide, sodium hydroxide, hydroxide Potassium, calcium hydroxide, sodium carbonate, sodium hydrogen carbonate and the like can be used.
  • These solid alkaline substances may be those generally used for foods and pharmaceuticals, and may be used alone or in combination of two or more.
  • sodium methoxide is preferably used.
  • a solid alkali substance having a weight ratio of 150 to 750 ppm is brought into contact with the glyceride fat that has undergone the decoloring and deodorizing steps.
  • SFC (20 ° C. and / or 35 ° C.) is in the range of 0.9 to 1.1 with respect to SFC (20 ° C. and / or 35 ° C.) of fats and oils when obtained without contact with solid alkaline substance It is difficult and unpreferable.
  • SFC (20 degreeC and / or 35 degreeC) of the obtained fats and oils is made without contacting a solid alkali substance.
  • the SFC (20 ° C. and / or 35 ° C.) of the fat when obtained is characterized by being in the range of 0.9 to 1.1, and by making it within this range, the physical properties of the fat and oil are greatly increased.
  • chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester, and glycidol fatty acid ester as a forming substance thereof in the glyceride oil can be reduced.
  • the above range is not substantially exceeded.
  • it can be controlled within the above range by a method such as shortening the contact time.
  • purification such as decolorization and deodorization is preferably performed, and either decolorization or deodorization may be performed, but both are preferably performed.
  • the shape of the solid alkaline substance used in the present invention is not particularly limited as long as it can be contacted in solid form, not in a solution dissolved in a solvent or the like. However, in order to make contact more efficiently, it is in a powder form. More preferably, a fine powder form containing 60 w / w% or more of particles having a particle size of 1.2 mm or less is suitable.
  • the method for contacting the solid alkaline substance is not particularly limited, but the method is to add the solid alkaline substance to the heated glyceride oil and fat, remove the solid alkaline substance by centrifugation after mixing and stirring for about 30 minutes.
  • the method is to add the solid alkaline substance to the heated glyceride oil and fat, remove the solid alkaline substance by centrifugation after mixing and stirring for about 30 minutes.
  • a prescribed amount of sodium methoxide is added to glyceride oil heated to 85 ° C. and reacted under vacuum. After stirring and centrifuging for the purpose of neutralization and washing with water, the oil layer is dehydrated, decolorized, and deodorized to reduce chloropropanols and substances forming the glyceride oil.
  • the glyceride fats and oils obtained by the method of the present invention have a reduced content of 3-chloropropanediol and 3-chloropropanediol fatty acid esters that are chloropropanols, and glycidol fatty acid esters that form the chloropropanols.
  • the content of propanols and glycidol fatty acid esters which are substances forming the propanols is measured by the following method with reference to the following literature. (Determination of total 3-chloropropane-1,2-diol (3-MCPD) in editable oils by cleavage of MCPD esters with sodium method. Eur. J. Lipid Sci.
  • the upper layer is subjected to GS-MS analysis.
  • GC-MS is quantified using molecular ion peaks m / z 196 (3-MCPD) and m / z 201 (3-MCPD-d 5 ).
  • the above method is adopted as a method for measuring 3-chloropropanediol fatty acid ester and glycidol fatty acid ester, which is a forming substance, in Germany (Deutsche Gesellchaft fur Fettsch: DGF). Hydrolyzes 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester in fats and oils, all 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester as 3-MCPD Measuring. “With this method, another compounds forming 3-MCPD under the conditions of the anomalous areal and detected three-MCPD esters”. (Ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and 3-MCPD forming subnets: DGF Standard Methods Section C-Fats / C-III 18 (09))
  • RBD palm olein (iodine value: 67) was added with 2% by weight of white clay, decolorized at 110 ° C. and 20 Torr for 10 minutes, and then deodorized at 250 ° C. and 2 Torr for 90 minutes.
  • the content of chloropropanols and the substances forming the edible palm olein was 6.1 ppm.
  • the SFC% is 25.5% at 20 ° C. (1.0 with respect to the SFC of the fat obtained in Comparative Example 2), and 6.2% at 35 ° C. (the SFC of the fat obtained in Comparative Example 2). 1.0), which was in the range of 0.9 to 1.1.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
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Abstract

Disclosed is a method wherein glyceride oil or fat after the bleaching and deodorizing step is brought into contact with an alkaline aqueous solution and then purified, thereby reducing chloropropanols such as 3-chloropropanediol or 3-chloropropanediol fatty acid esters and chloropropanol-forming substances in the glyceride oil or fat. Specifically disclosed is a method wherein when glyceride oil or fat after the bleaching and deodorizing step is brought into contact with a solid alkaline substance at a weight ratio of 150-750 ppm and then purified, the SFC (at 20˚C and/or 35˚C) of the oil or fat to be obtained is set to be 0.9-1.1 relative to the SFC (at 20˚C and/or 35˚C) of the oil or fat that is purified without being brought into contact with the solid alkaline substance. Consequently, chloropropanols such as 3-chloropropanediol or 3-chloropropanediol fatty acid esters and chloropropanol-forming substances in the glyceride oil or fat can be reduced.

Description

グリセリド油脂中のクロロプロパノール類及びその形成物質を低減する方法Method for reducing chloropropanols and substances formed in glyceride oils and fats
本発明はグリセリド油脂中のクロロプロパノール類及びその形成物質を低減する方法に関する。 The present invention relates to a method for reducing chloropropanols and substances forming the same in glyceride oils and fats.
クロロプロパノールとは、プロパノールに塩素が結合した物質の総称であるが、これらの一種である、３－クロロプロパンジオールは、従来から、しょうゆなど主にアミノ酸液を製造する際、副産物として少量生成することが知られており、また食品を加熱調理する過程で、脂質と食塩の存在により生成するといわれている。 Chloropropanol is a general term for substances in which chlorine is bonded to propanol, but 3-chloropropanediol, which is one of these substances, has conventionally been produced in small quantities as a by-product when mainly producing amino acid solutions such as soy sauce. In addition, it is said that it is formed by the presence of lipids and salt in the process of cooking food.
最近、食用油脂中には、少量の３－クロロプロパンジオールが脂肪酸と結合したエステル体で存在することがあると明らかになった。（非特許文献１） Recently, it has become clear that a small amount of 3-chloropropanediol may be present in edible fats and oils in the form of an ester combined with a fatty acid. (Non-Patent Document 1)
さらに、最近、グリセリド油脂中にクロロプロパノール類が生成される過程において、グリシドール脂肪酸エステルがその形成物質として存在していることも報告されている。（非特許文献２） Furthermore, recently, it has been reported that glycidol fatty acid esters are present as forming substances in the process of producing chloropropanols in glyceride oils. (Non-Patent Document 2)
３－クロロプロパンジオール脂肪酸エステルについては、許容摂取量が定められている、というような規制は無いが、欧州においては、３－クロロプロパンジオール脂肪酸エステルに結合する脂肪酸が全て遊離して、３－クロロプロパンジオールになるとみなし、評価をする動きがあり、グリセリド油脂中の含量を低減する技術の開発が望まれている。 For 3-chloropropanediol fatty acid ester, there is no regulation that the allowable intake is set, but in Europe, all the fatty acids bound to 3-chloropropanediol fatty acid ester are released and 3-chloropropanediol fatty acid ester is released. Therefore, there is a movement to evaluate, and development of a technique for reducing the content in glyceride fats is desired.
また、グリシドール脂肪酸エステルについても、毒性学的なデータはないが、クロロプロパノール類と同様、グリセリド油脂中の含量を低減する技術の開発が望まれている。 There is no toxicological data for glycidol fatty acid esters, but development of a technique for reducing the content in glyceride oils and fats is desired, as with chloropropanols.
本発明は、クロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルなどを低減する方法を提供することを目的とする。 An object of the present invention is to provide a method for reducing chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester and glycidol fatty acid ester which is a forming substance thereof.
本発明者らは、鋭意研究を重ねた結果、脱色、脱臭工程を経たグリセリド油脂をアルカリ水溶液と接触後、精製することにより、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減させることができるという知見を見出し、本発明を完成させるに至った。 As a result of intensive studies, the present inventors can reduce chloropropanols and their forming substances in glyceride oils and fats by purifying glyceride oils and fats that have undergone decolorization and deodorization processes after contacting with an alkaline aqueous solution. As a result, the present invention has been completed.
また、本発明者らは、鋭意研究を重ねた結果、脱色、脱臭工程を経たグリセリド油脂に重量比１５０～７５０ｐｐｍの固形アルカリ物質を接触させ、得られる油脂のＳＦＣ（２０℃及び／又は３５℃）を、固形アルカリ物質を接触させることなく得られる油脂のＳＦＣ（２０℃及び／又は３５℃）に対し、０．９～１．１の範囲内とすることにより、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減させることができるという知見を見出し、本発明を完成させるに至った。 Further, as a result of intensive research, the present inventors contacted a glyceride oil / fat that has undergone decoloring and deodorizing processes with a solid alkaline substance having a weight ratio of 150 to 750 ppm, and SFC (20 ° C. and / or 35 ° C.) of the obtained oil / fat. ) In the range of 0.9 to 1.1 with respect to the SFC (20 ° C. and / or 35 ° C.) of the fats and oils obtained without contacting the solid alkaline substance, chloropropanols in the glyceride fats and oils And the knowledge that the formation substance was able to be reduced was discovered, and it came to complete this invention.
すなわち本発明の第一は、脱色、脱臭工程を経たグリセリド油脂をアルカリ水溶液と接触後、精製することを特徴とする、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減する方法である。
第二は、アルカリ水溶液と接触後、グリセリド油脂の精製を２３０℃以下で行う第一記載の方法である。
第三は、アルカリ水溶液と接触後、精製前にグリセリド油脂を水洗する第一又は二記載のいずれかの方法である。
第四は、脱色、脱臭工程を経たグリセリド油脂に重量比１５０～７５０ｐｐｍの固形アルカリ物質を接触させ、得られる油脂のＳＦＣ（２０℃及び／又は３５℃）を、固形アルカリ物質を接触させることなく得られる油脂のＳＦＣ（２０℃及び／又は３５℃）に対し、０．９～１．１の範囲内とすることを特徴とする、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減する方法である。（ＳＦＣ：Ｓｏｌｉｄ　Ｆａｔ　Ｃｏｎｔｅｎｔ／固体脂指数）
第五は、固形アルカリ物質が粒子径１．２ｍｍ以下の粒子を６０重量％以上含有する粉末状である、第四記載の方法である。 That is, the first of the present invention is a method for reducing chloropropanols and their forming substances in glyceride fats and oils, wherein the glyceride fats and oils that have undergone decoloring and deodorizing steps are purified after contacting with an alkaline aqueous solution.
The second is the method described in the first, wherein the glyceride oil is purified at 230 ° C. or lower after contact with the alkaline aqueous solution.
The third method is either the first method or the second method in which the glyceride fat is washed with water after the contact with the alkaline aqueous solution and before purification.
Fourth, a solid alkaline substance with a weight ratio of 150 to 750 ppm is brought into contact with the glyceride fats and oils that have undergone the decoloring and deodorizing steps, and the SFC (20 ° C and / or 35 ° C) of the resulting fats and oils is brought into contact with the solid alkaline substances A method for reducing chloropropanols in glyceride fats and substances forming the same, characterized by being within a range of 0.9 to 1.1 with respect to SFC (20 ° C. and / or 35 ° C.) of the obtained fats and oils It is. (SFC: Solid Fat Content / solid fat index)
The fifth is the method according to the fourth, wherein the solid alkaline substance is in the form of a powder containing 60% by weight or more of particles having a particle diameter of 1.2 mm or less.
本発明の方法により、グリセリド油脂中のクロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルなどを低減することができる。 According to the method of the present invention, 3-chloropropanediol and 3-chloropropanediol fatty acid ester which are chloropropanols in glyceride fats and oils, and glycidol fatty acid ester which is a forming substance thereof can be reduced.
以下に、本発明を詳細に説明する。 The present invention is described in detail below.
本発明に用いられる油脂は、大豆油、菜種油、コーン油、綿実油、落花生油、ひまわり油、こめ油、ベニバナ油、サフラワー油、オリーブ油、ゴマ油、パーム油、ヤシ油、パーム核油等の植物性油脂並びに牛脂、豚脂等の動物脂、並びにこれらに分別、水素添加、エステル交換等を施した加工油脂の単品又は、これらを組み合わせたもので、脱色、脱臭の精製工程を経たグリセリド油脂であるが、これらのなかでもパーム系油脂に好ましく適用できる。 The oils and fats used in the present invention include soybean oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, rice bran oil, safflower oil, safflower oil, olive oil, sesame oil, palm oil, palm oil, palm kernel oil and other plants. Oils and fats such as beef tallow and pork tallow, and processed oils and fats that have been subjected to separation, hydrogenation, transesterification, etc., or a combination of these. Among them, among these, it can be preferably applied to palm oils.
本発明に用いられるアルカリ剤としては、アルカリ金属若しくはアルカリ土類金属の水酸化物、及び炭酸塩を用いることができ、具体的には、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸水素ナトリウム等を用いることができる。これらアルカリ剤は食品や医薬品用として一般に用いられているもので良く、単独あるいは２種以上を組み合わせて用いることができるが、これらのなかでも、水酸化ナトリウムを用いることが好ましい。 As the alkali agent used in the present invention, alkali metal or alkaline earth metal hydroxides and carbonates can be used, and specifically, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate. Sodium hydrogen carbonate or the like can be used. These alkaline agents may be those generally used for foods and pharmaceuticals, and may be used alone or in combination of two or more. Among these, sodium hydroxide is preferably used.
本発明の方法は、例えば、グリセリド油脂を水酸化ナトリウム水溶液と接触後、精製させる場合、７０℃に加熱したグリセリド油脂中に水酸化ナトリウム水溶液を規定量加え、攪拌、遠心分離後、油層を脱水し、脱色、脱臭を行うことにより、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減させることができる。 In the method of the present invention, for example, when a glyceride fat is purified after contacting with a sodium hydroxide aqueous solution, a prescribed amount of the sodium hydroxide aqueous solution is added to the glyceride fat heated to 70 ° C., and the oil layer is dehydrated after stirring and centrifuging. In addition, by performing decolorization and deodorization, chloropropanols and their forming substances in glyceride fats and oils can be reduced.
また、本発明の方法は、アルカリ水溶液と接触後、さらに脱色、脱臭の精製を行うことが好ましいが、この際の精製工程は２３０℃以下で行うと、よりグリセリド油脂中のクロロプロパノール類及びその形成物質を低減させる効果が得られ好ましい。 Further, the method of the present invention preferably further performs decolorization and deodorization purification after contact with the aqueous alkali solution. However, when the purification step at this time is carried out at 230 ° C. or lower, the chloropropanols in the glyceride oil and fat and its The effect of reducing the forming substance is obtained, which is preferable.
さらに、本発明の方法は、アルカリ水溶液と接触後、精製を行う前に水洗することにより、グリセリド油脂中のクロロプロパノール類及びその形成物質を、より低減させることができる。 Furthermore, the method of the present invention can further reduce chloropropanols and substances forming the same in glyceride fats and oils by washing with an aqueous alkali solution and before purification.
本発明に用いられる固形アルカリ物質としては、アルコキシド化合物、アルカリ金属若しくはアルカリ土類金属の水酸化物、及び炭酸塩を用いることができ、具体的には、ナトリウムメトキシド、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸水素ナトリウム等を用いることができる。これら固形アルカリ物質は食品や医薬品用として一般に用いられているもので良く、単独あるいは２種以上を組み合わせて用いることができるが、これらのなかでも、ナトリウムメトキシドを用いることが好ましい。 As the solid alkaline substance used in the present invention, alkoxide compounds, alkali metal or alkaline earth metal hydroxides, and carbonates can be used. Specifically, sodium methoxide, sodium hydroxide, hydroxide Potassium, calcium hydroxide, sodium carbonate, sodium hydrogen carbonate and the like can be used. These solid alkaline substances may be those generally used for foods and pharmaceuticals, and may be used alone or in combination of two or more. Among these, sodium methoxide is preferably used.
本発明において、脱色、脱臭工程を経たグリセリド油脂に対し、重量比１５０～７５０ｐｐｍの固形アルカリ物質を接触させるが、接触させる固形アルカリ物質が下限未満では、グリセリド油脂中のクロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルなどを十分に低減させることができず、上限を越えると、グリセリド油脂の物性変化に及ぼす影響が強くなり、得られる油脂のＳＦＣ（２０℃及び／又は３５℃）を、固形アルカリ物質を接触させることなく得られる場合の油脂のＳＦＣ（２０℃及び／又は３５℃）に対して、０．９～１．１の範囲内にすることが難しく、好ましくない。 In the present invention, a solid alkali substance having a weight ratio of 150 to 750 ppm is brought into contact with the glyceride fat that has undergone the decoloring and deodorizing steps. Chloropropanediol, 3-chloropropanediol fatty acid ester and glycidol fatty acid ester, which is a substance that forms them, cannot be reduced sufficiently. SFC (20 ° C. and / or 35 ° C.) is in the range of 0.9 to 1.1 with respect to SFC (20 ° C. and / or 35 ° C.) of fats and oils when obtained without contact with solid alkaline substance It is difficult and unpreferable.
また、本発明において、脱色、脱臭工程を経たグリセリド油脂に対し、固形アルカリ物質を接触させる際に、得られる油脂のＳＦＣ（２０℃及び／又は３５℃）を、固形アルカリ物質を接触させることなく得られる場合の油脂のＳＦＣ（２０℃及び／又は３５℃）に対して、０．９～１．１の範囲内にすることを特徴とし、この範囲内にすることにより、油脂の物性を大きく変化させることなく、グリセリド油脂中のクロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルなどを低減させることができる。 Moreover, in this invention, when making a solid alkali substance contact with the glyceride fats and oils which passed through the decoloring and deodorizing process, SFC (20 degreeC and / or 35 degreeC) of the obtained fats and oils is made without contacting a solid alkali substance. The SFC (20 ° C. and / or 35 ° C.) of the fat when obtained is characterized by being in the range of 0.9 to 1.1, and by making it within this range, the physical properties of the fat and oil are greatly increased. Without change, chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester, and glycidol fatty acid ester as a forming substance thereof in the glyceride oil can be reduced.
本発明において、得られる油脂のＳＦＣを０．９～１．１の範囲内にする方法としては、上記重量比１５０～７５０ｐｐｍの固形アルカリ物質を接触させる場合は、ほぼ上記範囲を越えることはないが、接触時間を短縮するなどの方法により、上記範囲内に制御することができる。 In the present invention, as a method of setting the SFC of the obtained fat and oil within the range of 0.9 to 1.1, when the solid alkali substance having a weight ratio of 150 to 750 ppm is contacted, the above range is not substantially exceeded. However, it can be controlled within the above range by a method such as shortening the contact time.
また、本発明において、固形アルカリ接触後、脱色、脱臭といった精製を行うことが好ましく、脱色あるいは脱臭のいずれかのみでもよいが、両方行うことが好ましい。 In the present invention, after contact with a solid alkali, purification such as decolorization and deodorization is preferably performed, and either decolorization or deodorization may be performed, but both are preferably performed.
本発明で使用する固形アルカリ物質は、溶媒等に溶解させた溶液状ではなく、固形で接触させることができれば、その形状は特に限定されないが、より効率よく接触させるためには、粉末状であることが好ましく、より好ましくは粒径１．２ｍｍ以下の粒子を６０ｗ／ｗ％以上含有する微粉末状が好適である。 The shape of the solid alkaline substance used in the present invention is not particularly limited as long as it can be contacted in solid form, not in a solution dissolved in a solvent or the like. However, in order to make contact more efficiently, it is in a powder form. More preferably, a fine powder form containing 60 w / w% or more of particles having a particle size of 1.2 mm or less is suitable.
本発明において、固形アルカリ物質の接触方法としては、特に限定されないが、加温したグリセリド油脂中に、固形アルカリ物質を添加し、約３０分間混合攪拌後、遠心分離により固形アルカリ物質を除去する方法などを挙げることができ、例えば、グリセリド油脂をナトリウムメトキシドと接触後、精製させる場合、８５℃に加熱したグリセリド油脂中にナトリウムメトキシドを規定量加え、真空下で反応させた後、酸及び水による中和、水洗を目的として攪拌、遠心分離後、油層を脱水し、脱色、脱臭を行うことにより、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減させることができる。 In the present invention, the method for contacting the solid alkaline substance is not particularly limited, but the method is to add the solid alkaline substance to the heated glyceride oil and fat, remove the solid alkaline substance by centrifugation after mixing and stirring for about 30 minutes. For example, when purifying glyceride oil after contact with sodium methoxide, a prescribed amount of sodium methoxide is added to glyceride oil heated to 85 ° C. and reacted under vacuum. After stirring and centrifuging for the purpose of neutralization and washing with water, the oil layer is dehydrated, decolorized, and deodorized to reduce chloropropanols and substances forming the glyceride oil.
本発明の方法によって得られたグリセリド油脂は、クロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルの含量が低減されるが、本発明において、クロロプロパノール類及びその形成物質であるグリシドール脂肪酸エステルの含量は以下の文献を参考に次のような方法で測定している。
（Ｄｅｔｅｒｍｉｎａｔｉｏｎ　ｏｆ　ｔｏｔａｌ　３－ｃｈｌｏｒｏｐｒｏｐａｎｅ－１，２－ｄｉｏｌ　（３－ＭＣＰＤ）　ｉｎ　ｅｄｉｂｌｅ　ｏｉｌｓ　ｂｙ　ｃｌｅａｖａｇｅ　ｏｆ　ＭＣＰＤ　ｅｓｔｅｒｓ　ｗｉｔｈ　ｓｏｄｉｕｍ　ｍｅｔｈｏｘｉｄｅ．　Ｅｕｒ．　Ｊ．　Ｌｉｐｉｄ　Ｓｃｉ．　Ｔｅｃｈｎｏｌ．　２００８，　１１０，：１８３－１８６） The glyceride fats and oils obtained by the method of the present invention have a reduced content of 3-chloropropanediol and 3-chloropropanediol fatty acid esters that are chloropropanols, and glycidol fatty acid esters that form the chloropropanols. The content of propanols and glycidol fatty acid esters which are substances forming the propanols is measured by the following method with reference to the following literature.
(Determination of total 3-chloropropane-1,2-diol (3-MCPD) in editable oils by cleavage of MCPD esters with sodium method. Eur. J. Lipid Sci.
すなわちまず、油脂　０．１ｇをｔ‐ブチルメチルエーテル　１ｍｌに溶かし、２０μｇ／ｍｌ内部標準物質（３－ＭＣＰＤ－ｄ５　酢酸エチル溶液）２５０μｌを加え、ＮａＯＣＨ３　溶液（０．５ｍｏｌ／ｌＮａＯＣＨ３　ｉｎ　ＭｅＯＨ）１ｍｌと混和後、室温で１０分静置する。
続いて、ヘキサン　３ｍｌ、ＮａＣｌ　溶液（ＮａＣｌ　２００ｇ／水　１ｌ）３ｍｌ、氷酢酸　０．１ｍｌを添加し、攪拌後、上層を除去する。
さらに、ヘキサン　３ｍｌを添加、攪拌後、上層を除去する。
そして、フェニルボロン酸溶液（フェニルボロン酸１ｇをアセトン：水＝１９：１　４ｍｌに溶解）を添加、攪拌後、８０℃、２０分放置し、室温に放冷後、ヘキサン　２ｍｌを添加、攪拌し、上層をＧＳ－ＭＳ分析に供する。
なお、ＧＣ－ＭＳについては、分子イオンピークｍ／ｚ　１９６（３－ＭＣＰＤ）、ｍ／ｚ　２０１（３－ＭＣＰＤ－ｄ５）を用いて定量する。 That is, first, 0.1 g of fat or oil was dissolved in 1 ml of t-butyl methyl ether, 250 μl of 20 μg / ml internal standard substance (3-MCPD-d 5 ethyl acetate solution) was added, and NaOCH 3 solution (0.5 mol / l NaOCH 3 in MeOH) was added. ) After mixing with 1 ml, let stand at room temperature for 10 minutes.
Subsequently, 3 ml of hexane, 3 ml of NaCl solution (NaCl 200 g / water 1 l) and 0.1 ml of glacial acetic acid are added, and after stirring, the upper layer is removed.
Furthermore, 3 ml of hexane is added, and after stirring, the upper layer is removed.
Then, a phenylboronic acid solution (1 g of phenylboronic acid was dissolved in acetone: water = 19: 1, 4 ml) was added and stirred, then left at 80 ° C. for 20 minutes, allowed to cool to room temperature, and then 2 ml of hexane was added and stirred. The upper layer is subjected to GS-MS analysis.
GC-MS is quantified using molecular ion peaks m / z 196 (3-MCPD) and m / z 201 (3-MCPD-d 5 ).
なお、上記方法は、ドイツ（Ｄｅｕｔｓｃｈｅ　Ｇｅｓｅｌｌｓｃｈａｆｔ　ｆｕｒ　Ｆｅｔｔｗｉｓｓｅｎｓｃｈａｆｔ：ＤＧＦ）の、３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルの測定方法として採用されているものであるが、この方法では、グリセリド油脂中の３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルを加水分解し、グリセリド油脂中に存在する３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルを全て３－ＭＣＰＤとして測定している。
「Ｗｉｔｈ　ｔｈｉｓ　ｍｅｔｈｏｄ，　ｏｔｈｅｒ　ｃｏｍｐｏｕｎｄｓ　ｆｏｒｍｉｎｇ　３－ＭＣＰＤ　ｕｎｄｅｒ　ｔｈｅ　ｃｏｎｄｉｔｉｏｎｓ　ｏｆ　ａｎａｌｙｓｉｓ　ａｒｅ　ａｌｓｏ　ｄｅｔｅｃｔｅｄ．　Ｔｈｅ　ｍｏｓｔ　ｉｍｐｏｒｔａｎｔ　３－ＭＣＰＤ　ｅｓｔｅｒｓ　ｆｏｒｍｉｎｇ　ｃｏｍｐｏｕｎｄｓ　ｉｓ　ｇｌｙｃｉｄｏｌ　（ｏｘｉｒａｎｅ－２－ｍｅｔｈａｎｏｌ）．」
（Ｅｓｔｅｒ－ｂｏｕｎｄ　３－ｃｈｌｏｒｏｐｒｏｐａｎｅ－１，２－ｄｉｏｌ（３－ＭＣＰＤ　ｅｓｔｅｒｓ）　ａｎｄ　３－ＭＣＰＤ　ｆｏｒｍｉｎｇ　ｓｕｂｓｔａｎｃｅｓ：ＤＧＦ　Ｓｔａｎｄａｒｄ　Ｍｅｔｈｏｄｓ　Ｓｅｃｔｉｏｎ　Ｃ－Ｆａｔｓ／Ｃ－ＩＩＩ　１８（０９）） The above method is adopted as a method for measuring 3-chloropropanediol fatty acid ester and glycidol fatty acid ester, which is a forming substance, in Germany (Deutsche Gesellchaft fur Fettwissenschaft: DGF). Hydrolyzes 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester in fats and oils, all 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester as 3-MCPD Measuring.
“With this method, another compounds forming 3-MCPD under the conditions of the anomalous areal and detected three-MCPD esters”.
(Ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and 3-MCPD forming subnets: DGF Standard Methods Section C-Fats / C-III 18 (09))
以下、実施例を示し、本発明をさらに具体的に説明する。なお、例中の％及びｐｐｍは重量基準を意味する。なおＳＦＣ：Ｓｏｌｉｄ　Ｆａｔ　Ｃｏｎｔｅｎｔ／固体脂指数の測定は、ＡＯＣＳ　Ｏｆｆｉｃｉａｌ　Ｍｅｔｈｏｄ　第５版Ｃｄ１６－８１に準じて行った。 Hereinafter, the present invention will be described more specifically with reference to examples. In the examples,% and ppm mean weight basis. In addition, the measurement of SFC: Solid Fat Content / solid fat index was performed according to AOCS Official Method 5th edition Cd16-81.
（比較例１）
ＲＢＤパームオレイン（ヨウ素価：６７）に、白土２重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、続いて、２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。
得られた食用パームオレイン中のクロロプロパノール類及びその形成物質の含量は、６．１ｐｐｍであった。 (Comparative Example 1)
RBD palm olein (iodine value: 67) was added with 2% by weight of white clay, decolorized at 110 ° C. and 20 Torr for 10 minutes, and then deodorized at 250 ° C. and 2 Torr for 90 minutes.
The content of chloropropanols and the substances forming the edible palm olein was 6.1 ppm.
ＲＢＤパームオレイン（ヨウ素価：６７）に１５％水酸化ナトリウム４重量％添加し、攪拌接触後、遠心分離する。水層は除去し、油層にイオン交換水２０重量％添加し、攪拌し、遠心分離する。水層を除去し、得られた油層を１１０℃、２０Ｔｏｒｒで１０分間脱水処理を行った。白土２重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、続いて、２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。
精製後の食用パームオレイン中のクロロプロパノール類及びその形成物質の含量は、３．９ｐｐｍであった。 4% by weight of 15% sodium hydroxide is added to RBD palm olein (iodine value: 67), and after stirring and contact, centrifuged. The aqueous layer is removed, 20% by weight of ion-exchanged water is added to the oil layer, and the mixture is stirred and centrifuged. The aqueous layer was removed, and the resulting oil layer was dehydrated at 110 ° C. and 20 Torr for 10 minutes. 2% by weight of white clay was added, and decolorization was performed at 110 ° C. and 20 Torr for 10 minutes, followed by deodorization treatment at 250 ° C. and 2 Torr for 90 minutes.
The content of chloropropanols and their forming substances in the edible palm olein after purification was 3.9 ppm.
ＲＢＤパームオレイン（ヨウ素価：６７）に１５％水酸化ナトリウム４重量％添加し、攪拌接触後、遠心分離する。水層は除去し、油層にイオン交換水２０重量％添加し、攪拌し、遠心分離する。水層を除去し、得られた油層を１１０℃、２０Ｔｏｒｒで１０分間脱水処理を行った。白土２重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、続いて、２２０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。
精製後の食用パームオレイン中のクロロプロパノール類及びその形成物質の含量は、２．３ｐｐｍであった。 4% by weight of 15% sodium hydroxide is added to RBD palm olein (iodine value: 67), and after stirring and contact, centrifuged. The aqueous layer is removed, 20% by weight of ion-exchanged water is added to the oil layer, and the mixture is stirred and centrifuged. The aqueous layer was removed, and the resulting oil layer was dehydrated at 110 ° C. and 20 Torr for 10 minutes. 2% by weight of white clay was added, and decolorization was performed at 110 ° C. and 20 Torr for 10 minutes, followed by deodorization treatment at 220 ° C. and 2 Torr for 90 minutes.
The content of chloropropanols and their forming substances in the edible palm olein after purification was 2.3 ppm.
（比較例２）
粗パーム油を脱色、脱臭して得られた精製パーム油（ヨウ素価：５２）に、白土２重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、続いて、２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。
得られた食用パーム油中のクロロプロパノール類及びその形成物質の含量は、６．５ｐｐｍであった。また、ＳＦＣ％は２０℃で２５．４％、３５℃で６．１％であった。 (Comparative Example 2)
2% by weight of white clay is added to refined palm oil (iodine value: 52) obtained by decolorizing and deodorizing crude palm oil, and decolorized at 110 ° C. and 20 Torr for 10 minutes, followed by 250 ° C. and 2 Torr for 90 minutes. Deodorization treatment was performed.
The content of chloropropanols and the substances forming the edible palm oil was 6.5 ppm. The SFC% was 25.4% at 20 ° C and 6.1% at 35 ° C.
粗パーム油を脱色、脱臭して得られた精製パーム油（ヨウ素価：５２）に粒径１ｍｍ以下の粒子を９６．６重量％以上含有する微粉末状のナトリウムメトキシドを３００ｐｐｍ添加し、真空下、８５℃で３０分間接触させた。その後油層に５０％クエン酸水溶液５重量％及びイオン交換水５０重量％を添加し、攪拌後、遠心分離した。水層を除去し、得られた油層を１１０℃、２０Ｔｏｒｒで１０分間脱水処理を行った後、白土２重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、続いて、２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。
精製後の食用パーム油中のクロロプロパノール類及びその形成物質の含量は、３．６ｐｐｍであった。また、ＳＦＣ％は２０℃で２５．５％（比較例２で得られた油脂のＳＦＣに対して１．０）、３５℃で６．２％（比較例２で得られた油脂のＳＦＣに対して１．０）であり、０．９～１．１の範囲内であった。 300 ppm of finely powdered sodium methoxide containing 96.6% by weight or more of particles having a particle size of 1 mm or less is added to purified palm oil (iodine value: 52) obtained by decolorizing and deodorizing crude palm oil, and vacuum Then, contact was made at 85 ° C. for 30 minutes. Thereafter, 5% by weight of 50% citric acid aqueous solution and 50% by weight of ion-exchanged water were added to the oil layer, followed by stirring and centrifugation. The aqueous layer was removed, and the resulting oil layer was dehydrated at 110 ° C. and 20 Torr for 10 minutes. Then, 2% by weight of white clay was added, and decolorized at 110 ° C. and 20 Torr for 10 minutes, followed by 250 ° C. and 2 Torr. Deodorization treatment was performed for 90 minutes.
The content of chloropropanols and their forming substances in the edible palm oil after purification was 3.6 ppm. The SFC% is 25.5% at 20 ° C. (1.0 with respect to the SFC of the fat obtained in Comparative Example 2), and 6.2% at 35 ° C. (the SFC of the fat obtained in Comparative Example 2). 1.0), which was in the range of 0.9 to 1.1.
（比較例３）
粗パーム油を脱色、脱臭して得られた精製パーム油（ヨウ素価：５２）に実施例１と同じナトリウムメトキシド粉末１５００ｐｐｍ添加し、真空下、８５℃で３０分間接触させた。その後油層に５０％クエン酸水溶液５重量％及びイオン交換水５０重量％添加し、攪拌し、遠心分離した。水層を除去し、得られた油層を１１０℃、２０Ｔｏｒｒで１０分間脱水処理を行った後、白土２重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、続いて、２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。
精製後の食用パーム油中のクロロプロパノール類及びその形成物質の含量は、２．４ｐｐｍであった。ただし、ＳＦＣ％は２０℃で３８．３％（比較例２で得られた油脂のＳＦＣに対して１．５）、３５℃で１２．３％（比較例２で得られた油脂のＳＦＣに対して２．０）であり、０．９～１．１の範囲外であった。 (Comparative Example 3)
1500 ppm of the same sodium methoxide powder as in Example 1 was added to purified palm oil (iodine value: 52) obtained by decolorizing and deodorizing the crude palm oil, and contacted at 85 ° C. for 30 minutes under vacuum. Thereafter, 5% by weight of 50% aqueous citric acid solution and 50% by weight of ion-exchanged water were added to the oil layer, and the mixture was stirred and centrifuged. The aqueous layer was removed, and the resulting oil layer was dehydrated at 110 ° C. and 20 Torr for 10 minutes. Then, 2% by weight of white clay was added, and decolorized at 110 ° C. and 20 Torr for 10 minutes, followed by 250 ° C. and 2 Torr. Deodorization treatment was performed for 90 minutes.
The content of chloropropanols and the forming substances in the edible palm oil after purification was 2.4 ppm. However, the SFC% is 38.3% at 20 ° C. (1.5 with respect to the SFC of the oil obtained in Comparative Example 2), and 12.3% at 35 ° C. (the SFC of the oil obtained in Comparative Example 2). 2.0) and out of the range of 0.9 to 1.1.
粗パーム油を脱色、脱臭して得られた精製パーム油（ヨウ素価：５２）に粒径０．７ｍｍ以下の粒子を６０重量％以上含有する粉末状の水酸化ナトリウムを３００ｐｐｍ添加し、真空下、８５℃で３０分間接触させた。その後油層に５０％クエン酸水溶液５重量％及びイオン交換水５０重量％添加し、攪拌し、遠心分離した。水層を除去し、得られた油層を１１０℃、２０Ｔｏｒｒで１０分間脱水処理を行った後、白土２重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、続いて、２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。
精製後の食用パーム油中のクロロプロパノール類及びその形成物質の含量は、５．９ｐｐｍであった。また、ＳＦＣ％は２０℃で２５．７％（比較例２で得られた油脂のＳＦＣに対して１．０）、３５℃で５．８％（比較例２で得られた油脂のＳＦＣに対して０．９５）であり、０．９～１．１の範囲内であった。 300 ppm of powdered sodium hydroxide containing 60% by weight or more of particles having a particle size of 0.7 mm or less was added to refined palm oil (iodine value: 52) obtained by decolorizing and deodorizing crude palm oil, and under vacuum For 30 minutes at 85 ° C. Thereafter, 5% by weight of 50% aqueous citric acid solution and 50% by weight of ion-exchanged water were added to the oil layer, and the mixture was stirred and centrifuged. The aqueous layer was removed, and the resulting oil layer was dehydrated at 110 ° C. and 20 Torr for 10 minutes. Then, 2% by weight of white clay was added, and decolorized at 110 ° C. and 20 Torr for 10 minutes, followed by 250 ° C. and 2 Torr. Deodorization treatment was performed for 90 minutes.
The content of chloropropanols and the substances forming the edible palm oil after purification was 5.9 ppm. Moreover, SFC% is 25.7% at 20 ° C. (1.0 with respect to the SFC of the fat obtained in Comparative Example 2), and 5.8% at 35 ° C. (the SFC of the fat obtained in Comparative Example 2). And 0.95), which was in the range of 0.9 to 1.1.

Claims (5)

  1. 脱色、脱臭工程を経たグリセリド油脂をアルカリ水溶液と接触後、精製することを特徴とする、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減する方法。 A method for reducing chloropropanols in a glyceride oil and its formation substances, wherein the glyceride oil and fat which have undergone decoloring and deodorizing steps are purified after contacting with an alkaline aqueous solution.
  2. アルカリ水溶液と接触後、グリセリド油脂の精製を２３０℃以下で行う請求項１記載の方法。 The method of Claim 1 which refine | purifies glyceride fats and oils at 230 degrees C or less after contact with aqueous alkali solution.
  3. アルカリ水溶液と接触後、精製前にグリセリド油脂を水洗する請求項１又は２記載のいずれかの方法。 The method according to claim 1 or 2, wherein the glyceride fat is washed with water after the contact with the alkaline aqueous solution and before purification.
  4. 脱色、脱臭工程を経たグリセリド油脂に重量比１５０～７５０ｐｐｍの固形アルカリ物質を接触させ、得られる油脂のＳＦＣ（２０℃及び／又は３５℃）を、固形アルカリ物質を接触させることなく得られる油脂のＳＦＣ（２０℃及び／又は３５℃）に対し、０．９～１．１の範囲内とすることを特徴とする、グリセリド油脂中のクロロプロパノール類及びその形成物質を低減する方法。（ＳＦＣ：Ｓｏｌｉｄ　Ｆａｔ　Ｃｏｎｔｅｎｔ／固体脂指数） A solid alkaline substance having a weight ratio of 150 to 750 ppm is brought into contact with a glyceride fat that has undergone decoloring and deodorizing processes, and SFC (20 ° C. and / or 35 ° C.) of the resulting fat is obtained without bringing the solid alkaline substance into contact. A method for reducing chloropropanols and substances forming the same in glyceride fats and oils, characterized by being within a range of 0.9 to 1.1 with respect to SFC (20 ° C and / or 35 ° C). (SFC: Solid Fat Content / solid fat index)
  5. 固形アルカリ物質が粒子径１．２ｍｍ以下の粒子を６０重量％以上含有する粉末状である、請求項４記載の方法。 The method according to claim 4, wherein the solid alkaline substance is in a powder form containing particles having a particle diameter of 1.2 mm or less in an amount of 60% by weight or more.
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